Ethanol → 6-Fluoro-6-methylheptan-1-ol

HRID 1654301Notes

Reaction equation

HRID 1654301 reaction equation
[F:1]C1OC(OC2(CCCCCC(C)C)CCCC(F)O2)(CCCCCC(C)C)CCC1.[C:32]1([CH3:42])[CH:37]=C[C:35](S([O-])(=O)=O)=[CH:34][CH:33]=1.[NH+]1C=CC=CC=1.[CH3:49][CH2:50][OH:51]>>[F:1][C:32]([CH3:42])([CH3:37])[CH2:33][CH2:34][CH2:35][CH2:49][CH2:50][OH:51]

Participants

4

Reactant 3

HCID 702EthanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 677982696-Fluoro-6-methylheptyl-2-tetrahydropyranyl ether

Product 1

HCID 104870116-Fluoro-6-methylheptan-1-ol

Procedure

A stirred solution of the product from Step I (3.34 g, 0.0144 mol) in absolute EtOH was treated with pyridinium p-toluenesulfonate (0.47 g, 0.00187 mol) and kept under nitrogen at ambient temperature for 41 hours. The mixture was concentrated and the residue, dissolved in EtOAc, was washed with aqueous NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel with 5 to 20% EtOAc-hexane to give 1.86 g of 6-fluoro-6-methyl -1-heptanol.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue, dissolved in EtOAc
  3. washwas washed with aqueous NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with 5 to 20% EtOAc-hexane

Sources & evidence

ORD record
ord-04548b32d0794db2b9a23d68f79dc3f0
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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